


Platonic best friend punishment time!

by zation



Series: SPN Kink Bingo 2018 [4]
Category: Supernatural
Genre: Alternate Universe - High School, Betting, Boys Being Boys, Dean Has a Crush, Dean in Panties, M/M, Masturbation, Masturbation in panties, Panty Kink, Plot What Plot/Porn Without Plot, Punishment Game, Some Humor, Supernatural Kink Bingo 2018
Language: English
Status: Completed
Published: 2018-06-14
Updated: 2018-06-14
Packaged: 2019-05-21 09:26:40
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,957
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14912777
Author URL: https://archiveofourown.org/users/zation/pseuds/zation
Summary: Annoyed that he lost last time he betted his best friend Cas on who could hold it the longest while jerking it, Dean proposes a new bet, determined not to lose this time and suffer the punishment.Or,The one where Dean totally loses but doesn’t suffer through the punishment as much as he thought he would.





	Platonic best friend punishment time!

**Author's Note:**

> Kinda a continuation of my other one-shot [Platonic best friend fun time!](https://archiveofourown.org/works/8952181) but there is absolutely no need to read that one first, both of these are basically PWPs anyway lol
> 
>  
> 
> **Square filled: Panty Kink**

 

“Get the cup.” Dean hisses through clenched teeth. “The fucking  _cup_.”

Cas is quick to hand it over but with how close Dean is to coming it’s not like he’s got brainpower enough left to manage to hold the cup and not spill. What ultimately throws him over the edge is Cas moving closer so that he can angle the cup to receive Dean’s spunk but Dean’s not going to say that.

No, the fact that he’s been jerking off to thoughts of his best friend coming his brains out all over the dining room table is something that he’ll be taking to his grave, thank you very much.

He shudders through his orgasm, images of Cas doing the same thing just thirty minutes earlier flashing before his inner eye and heightening his release. Cas hadn’t needed someone to hold his cup, though, that was for fucking sure. No, he’d just grunted and held it still to collect his jizz like a badass. Fuck yeah, Cas looks awesome when he comes, face all flushed and pretty mouth open almost as if he _wants_ Dean to stuff his dick in there. God _damn_.

Cas makes a contemplative sound when Dean’s done shaking the last few drops from his dickhead. He holds the cup up, way too close to his face for Dean not to imagine new, even lewder, things.

“It’s as if you don’t even want to compete, Dean.”

That sure as hell jerks Dean right out of his post-orgasmic haze.

“The fuck?”

Cas picks up his own measuring cup, holding the two side by side with a shit-eating grin and goddamnit, Dean doesn’t even need him to say it because he can see fine by himself. But Cas is obviously proud over this.

“Barely two milliliters, Dean.” He tuts and Dean grits his teeth. Fuck, he’d known it was a bad idea to jerk off yesterday but Cas had come over and they’d horsed around in the pool out back and yeah…

“We should do best out of three.”

“Or you should man up and take your punishment.” Cas grins and thankfully puts down the measuring cups. “That was the deal.”

“Yeah, yeah.” Dean mutters morosely, glaring at the innocent cups. Fuck Cas for coming almost twice as much as him, the difference is too visible. “You know you only came more because you’re a hopeless virgin with blue balls.”

“Not a virgin.” Cas grits and Dean regrets bringing it up because he kind of hates hearing about how Cas has already lost his virginity to some bimbo or whatever.

“Whatever, gimmie the punishment already.”

Fuck Dean feels annoyed. Not only because he’s lost (again!) but because now he’s also lost a great opportunity to use the punishment to get Cas to do something sweet. He hadn’t even decided on what to choose because the possibilities had seemed endless. And now he gets nothing and all because he hadn’t been able to keep his paws off his dick for a day. He supposes this is what they call divine justice or some shit like that.

“Well,” Cas hums thoughtfully, tapping his chin and looking up at the ceiling. “We tested who could hold it and you had no control over your orgasm, just like a girl.” Dean thinks that sounds highly unfair, first of all Cas hadn’t been far behind and second, Dean’s slept with a few women who were in definite control of their orgasms.

“Please, rub it in more.” He grouses and Cas looks at him with a twinkle in his (beautifully) blue eyes.

“We haven’t measured dicks, but yours is shorter than mine.”

“What the fuck’s that got to do with this?” Dean splutters, more because of the thought of Cas noticing Dean’s dick than him being angry. “And I’m thicker than you.”

Cas just grins. “And now you definitely came less than me, which certainly has made you on edge.” He fake-pouts and Dean’s eyes are instantly drawn to his mouth. “Is someone feeling like less of a man?”

“No!” Dean exclaims and watches with annoyance how Cas doubles over laughing at him. “Fuck you.”

“I’m just teasing you, Dean.” Cas grins and fuck him for being so fucking handsome. Dean mutters to himself and stuffs his dick back in his pants. “I mean, you tease me all the time and I’m starting to see why. This is fun!”

It’s not fun—okay, it’s kinda fun. Dean would probably never shut up about it if he had been in Cas’ shoes… but the fact is that Dean is kind of crushing pretty hard on his best friend and he wants to look cool. Not lose every goddamn sex bet he proposes.

“Punishment.” He snaps and Cas’ grin only widens. Dean gets a thrill at seeing Cas look mischievous like that but he still feels dread at the thought of what his friend’s come up with.

“Well, since you’re acting like a little girl, how about you dress the part?”

“What?” Dean frowns. “I ain’t putting on a dress and going outside, Cas.”

“Oh no.” Cas leans in, face in Dean’s and fuck Dean’s already spent dick for perking up. “I was thinking of something more subtle.” He grins again, obviously very satisfied with himself. “How about, as punishment for taunting me with how _easily_ you were going to win, you wear a pair of panties for a whole day? At school.”

Dean’s whole body goes rigid. “I… I don’t _have_ a pair of-of panties.”

Cas’ grin turns sly and Dean realizes that he’s caught in this trap and there’s no way out. “Don’t worry, Dean. I’ll provide.”

Dean gulps. Goddamn these bets and _goddamn_ his big mouth.

 

*****

 

Dean squirms in his seat, hyperaware of the panties Cas had brought him yesterday. They’re new, bought the same day and Dean gets sweaty just thinking about Cas going into a store and casually picking out a pair of panties for Dean to wear.

He’d even told Dean that he’d picked the peachy color because he thought it would complement Dean’s skin very well and Dean can’t even… he, he just _can’t_.

They’re made of a sleek satin material, cool on his skin, and along the edge there’s the barest hint of frill. They’re actually very pretty and if Dean had seen these on a woman he would definitely be interested. Sure, _he_ looks stupid in them but that isn’t the panties’ fault. That’s just because he’s a stocky guy with hips nowhere near as narrow as Cas has told him they are. Though he did manage to pick out the right size without even asking Dean so that’s got to count for something, Dean supposes as he grits himself through the morning.

He’s thankful that Cas at least chose today for him to wear the panties. Thursdays are pretty laid back in their schedule and Dean had for a moment feared that Cas would pick Tuesday when they have gym class but Cas isn’t cruel like that and Dean appreciates it.

Still, he’s wearing the jeans with the highest waist he could find in his closet and his biggest sweater, all of which to make sure he doesn’t accidentally show off the panties.

And all of that is well and good but it doesn’t explain _why in the fuck he’s hard_. Because _why_? Why would he get hard just sitting at his desk, listening to a boring History lecture, just because he happens to have a pair of women’s underwear on? It doesn’t make any goddamn sense and yet that’s what’s happening and it’s definitely the panties.

It’s just so _lewd_.

So lewd that he, a teenage boy, slipped into a pair of panties this morning that his best friend (his _mancrush_ ) has bought for him. And Cas _knows_ too. Knows that Dean has the panties on and Dean has caught him watching Dean’s hunched form on a number of occasions already. And that only makes Dean harder, knowing that Cas is watching.

Fuck, it’s enough to make his balls tremble with the need for release and he eyes the clock over the door anxiously. With every movement he can feel the panties dragging over his dick and he’s blurted out enough precome now that the satin sticks to the head and it _feels so good_.

He practically bolts for the restroom when the bell rings for lunch. Fuck, he’s a sweaty mess and he needs to jerk off. He’s not gonna mess up the punishment and take off the panties but he just needs to release some of the tension or he’s gonna burn up. Not even his grandpa jeans are enough to hide his erection now and he bows his head, keeping his backpack in front of him as he pushes through the throngs of students.

He flies up the stairs to the fourth floor where he knows fewer classes are taught and he’ll run less risk of running into someone. The restroom he chooses is at the far end of a corridor and it only has two stalls and three urinals, all of which are unoccupied.

He grunts in relief when he has locked the stall door and plopped down on the toilet. He takes a moment to just massage his dick through his jeans, head thrown back and eyes closed as he enjoys the feeling of the satin wrapping around his whole length.

He startles so badly he almost falls off the toilet when his phone goes off, the text message sound overly loud in the quiet restroom. He wants to ignore it but something in his gut tells him not to and just as he’s pulling his cell out of his pocket it dings again.

It’s of course from Cas.

 **[Cas]:** Where did you go?

 **[Cas]:** We have lunch now.

Dean grits his teeth because he _knows_ that and fuck you, dick, Cas using proper punctuation in a text message is _not_ a turn-on. Dean’s dick definitely disagrees.

 **[Me]:** not going I’m on the crapper

There, that’s disgusting enough that Cas ought to leave it. Knowing Cas, though…

 **[Cas]:** Are you okay?

Jesus fuck, Dean has to start palming himself again when he thinks about Cas’ concerned little frown. He unbuttons his jeans one-handedly and groans loudly when he puts his hand over his dick, still trapped in those fucking panties.

 **[Me]:** leave me alone k

Just as he’s sending that, he gets another text from Cas and this guy doesn’t take a hint.

 **[Cas]:** I thought you looked sweaty all morning. I figured it was because you were nervous about anyone finding out about the panties but I guess not?

Dean moans and the sound echoes off the restroom’s tiled walls. He jerks his dick through the panties, loving the feeling of the satin on his heated skin.

 **[Cas]:** And I will not “leave you alone”, Dean.

Fuck, Cas is sure to be squinting in annoyance at his phone now and he looks so fucking good when he does that. Dean looks down and makes an embarrassingly keening sound when he sees that he’s gotten too big for the panties to contain him and the head of his dick is poking out over the edge.

 **[Cas]:** I’m concerned, Dean. Which restroom are you in?

Fuck no, Dean’s not going to answer that and he’s just about to text back to Cas when the door outside his stall opens. He gasps in surprise, his dick throbbing in his hand, and he grips his phone hard in the other, trembling at the prospect of getting caught jerking off in panties while getting off to his best friend being concerned about his well-being.

“Is it this one?”

 _What the fuck is even going on?!_ Dean can’t _believe_ that Cas is outside his stall, he fucking chose the one the furthest away from people! It’s like Cas can read his freaking mind or something.

“Get out, Cas.” He smacks his hand against his face because how stupid wasn’t that? Why the hell did he even answer? Cas would probably not have checked the stalls like a creeper. Too late does he realize it’s the same hand that had moments ago cupped his wet dick and now he’s probably got precome on his face.

“Dean?” of course Cas stops right outside Dean’s stall. “Are you truly ill?”

Dean sighs, his arousal making him too on edge to lie. Also, he can’t do that to Cas because he’s always so caring of Dean that it would be cruel to make him worry unnecessarily.

“No.” He grunts as he pockets his phone, rubbing his dick in the process. “But I’m mad at you so go away.”

Cas shuffles in place for a moment and then the door thuds as if he’s put his hand on it. “Are you really mad, Dean?” he asks, his voice suddenly much lower. “Or are you aroused because of the panties?”

Dean’s mouth feels dry. How the fuck does he _know_? “The… the second one.”

“Dean…”

“Are we alone, Cas?”

He hears Cas walking away and then the sound of the outer door being locked. “Yes.”

Dean lets out a shuddering breath before he reaches forward and unlatches the door. It swings open slowly to reveal Cas just outside. He looks at Dean with dark eyes and Dean leans back on the toilet, spreading his legs and showing off the mess that is his wet panties and hard dick. He swallows slowly, feeling arousal spiked with adrenaline shoot through him. He’s both afraid that Cas will be disgusted and turn away and hopeful that he’ll like it and stay.

Cas takes one look on Dean’s dick and steps into the stall, looming over Dean with an expression Dean’s never seen on his normally so kind friend’s face. He looks positively wild and Dean for some reason loves it.

“I ruined the panties.” He almost pants and Cas’ eyes gleam.

“So you did.” He murmurs in a low rumble. “And you don’t even look finished, Dean.”

Dean gulps and presses the heel of his hand against his balls. They’re still completely trapped in the panties and he loves how well he fills them. The fabric is stretched taut and he’s almost slipping out a bit at the sides.

“It… it feels so good, Cas.”

“The panties?”

“Yeah.” He sighs out a moan and starts stroking himself right there in front of Cas. Well, he can leave if he doesn’t want to watch. Dean wants him to stay and see everything but he’s not going to ask. He is, however, going to fuck up into his hand and moan like a bitch in heat while he stares straight at Cas’ face.

His friend’s expression remains mostly stoic. His eyes track Dean’s every movement, though, and fucking hell it’s so hot. So fucking sexy how Cas just stands there and watches Dean stain the pretty panties he bought for him.

“Do you like how smooth they are?” Cas suddenly asks, his voice like whisky on the rocks and Dean arches his back.

“Y-yeah.” He moans and presses his thumbnail against the slit at the dickhead, feeling pleasure roll through him at the slightly stinging sensation.

“You haven’t taken your dick out.”

No, not fully. Instead he remains trapped in the panties, pressed up against his stomach, his palm dragging along his length even as his other hand massages his balls.

“No, I like it like this.”

“Yes.” Cas hisses and Dean’s orgasm makes itself known because fucking hell, he can’t take Cas looking at him like this while the panties rub against him and not come. “Next time maybe we try a pair with lace?”

Dean goes off with a strangled shout, coming like a freight train and completely soaking the panties. He groans and shudders through it, eyes closed and mouth open as he pants like a fucking dog. When he comes to enough to relax back against the toilet and open his eyes he finds the stall empty. His tongue clicks against the roof of his mouth but he doesn’t have time to call out for Cas before he appears in the stall again, a handful of napkins in his outstretched hand.

He smiles kindly at Dean. “I wetted them a little.”

Dean accepts them with a grunt and starts to try and salvage what he can but damn, he came a lot and all fucking over himself.

“I have to take them off.” He mutters and Cas nods, holding out his hand again.

“Give them to me. I’ll clean them in the sink while you dry off.”

“But…” Dean has to work _really fucking hard_ to ignore how his chest warms at Cas taking care of him right now. “The punishment…”

Cas’ handsome face splits in a wide grin. “Oh Dean, you just gave me something _much_ more precious than simply watching you squirm in the panties. I’m satisfied with this.”

Dean blushes beet red and mumbles something that’s supposed to be clever but certainly doesn’t feel like it. And when Cas comes in to fucking _help him_ get out of the panties he really can’t help how that warm feeling spreads throughout his body.

“I want black lace.” He states in an intimate murmur and Cas stops for a moment before turning up his face to give Dean a sweet smile.

“Sure.”

Yeah, Dean’s suddenly not so annoyed with losing that bet anymore. Cas looks fucking gorgeous cleaning up Dean’s mess and by the look on his face (and the tightness of his jeans) Dean would say that Cas likes it too.

“With a bow.”

“Anything you want, Dean.”

Fuck yeah, Dean’s starting to think he might just get that.

 

 

 


End file.
